US3301867A - Novel pyridoindoles - Google Patents

Novel pyridoindoles Download PDF

Info

Publication number
US3301867A
US3301867A US321661A US32166163A US3301867A US 3301867 A US3301867 A US 3301867A US 321661 A US321661 A US 321661A US 32166163 A US32166163 A US 32166163A US 3301867 A US3301867 A US 3301867A
Authority
US
United States
Prior art keywords
novel
pyridoindoles
pyrido
methoxy
indole
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US321661A
Other languages
English (en)
Inventor
Szmuszkovicz Jacob
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Upjohn Co filed Critical Upjohn Co
Priority to US321661A priority Critical patent/US3301867A/en
Priority to GB40907/64A priority patent/GB1069717A/en
Priority to CH1318964A priority patent/CH437328A/de
Priority to FR1565306D priority patent/FR1565306A/fr
Priority to NL6412919A priority patent/NL6412919A/xx
Application granted granted Critical
Publication of US3301867A publication Critical patent/US3301867A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the compounds of this invention include 1-styryland 1-phenethyl-6-methoxy-9H-pyrido[3,4-b1indoles of the formula omow N N wherein R is vinylene or ethylene, and the physiologically acceptable acid addition salts thereof, such asthe hydrochloride, hydrobromide, acetate, pyruvate, sulfate, phosphate, citrate, tartrate, salicylate, lactate, succinate benzoate, nitrate, p-toluenesulfonate and the like.
  • the compounds of this invention demonstrate significant depressant activity and can be administered to humans and animals as the primary active ingredient of conventional pharmaceutical forms such as tablets, capsules, elixirs, injectable solutions and suspensions and the like for tranquilization. These compounds are also active as anti-parasitic, anti-inflammatory, anorexigenic and analgesic agents. Additionally, the free bases form salts with fluosilicic acid which are useful as mothproofing agents in accord with U.S. Patent 1,915,334 and 2,075,359.
  • EXAMPLE 2 1 -phenethy l-6-methoxy-9H -py rido [3 ,4-b] indole
  • EXAMPLE 3 1-phenethyl-6-methoxy-9H-pyrido[3,4-b1indole hydrochloride
  • the product of Example 2 was dissolved in ether and converted to the hydrochloride 'with ethereal hydrogen chloride; 4.9 gm. (85% yield), M.P. 258-259 C. (dec.). Crystallization from methanol-ether afforded yellow rods, M.P. 258.5-259.5 C.
  • Ultraviolet spectrum (ethanol) showed Amax. 234 (26,150); 261 (20,750); 297 (16,750); 309 (18,450); sh. 376 (3,150); 400 (3,850).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US321661A 1963-11-06 1963-11-06 Novel pyridoindoles Expired - Lifetime US3301867A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US321661A US3301867A (en) 1963-11-06 1963-11-06 Novel pyridoindoles
GB40907/64A GB1069717A (en) 1963-11-06 1964-10-07 Improvements in or relating to pyrido[3,4-b]indole derivatives
CH1318964A CH437328A (de) 1963-11-06 1964-10-12 Verfahren zur Herstellung von neuen Indolderivaten
FR1565306D FR1565306A (de) 1963-11-06 1964-11-05
NL6412919A NL6412919A (de) 1963-11-06 1964-11-06

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US321661A US3301867A (en) 1963-11-06 1963-11-06 Novel pyridoindoles

Publications (1)

Publication Number Publication Date
US3301867A true US3301867A (en) 1967-01-31

Family

ID=23251474

Family Applications (1)

Application Number Title Priority Date Filing Date
US321661A Expired - Lifetime US3301867A (en) 1963-11-06 1963-11-06 Novel pyridoindoles

Country Status (5)

Country Link
US (1) US3301867A (de)
CH (1) CH437328A (de)
FR (1) FR1565306A (de)
GB (1) GB1069717A (de)
NL (1) NL6412919A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4120963A (en) * 1976-06-16 1978-10-17 Boehringer Mannheim Gmbh Certain pyrido[3,4-b]indole-1-ones
EP1134221A1 (de) * 2000-03-15 2001-09-19 Aventis Pharma Deutschland GmbH Substituierte beta-Carboline als lkB-Kinasehemmer

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4120963A (en) * 1976-06-16 1978-10-17 Boehringer Mannheim Gmbh Certain pyrido[3,4-b]indole-1-ones
EP1134221A1 (de) * 2000-03-15 2001-09-19 Aventis Pharma Deutschland GmbH Substituierte beta-Carboline als lkB-Kinasehemmer

Also Published As

Publication number Publication date
CH437328A (de) 1967-06-15
GB1069717A (en) 1967-05-24
FR1565306A (de) 1969-05-02
NL6412919A (de) 1965-05-07

Similar Documents

Publication Publication Date Title
DE1080563B (de) Verfahren zur Herstellung diquaternaerer Salze von Alkylendiaminen
EP0000220A1 (de) Dihydrouracile, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
US3301867A (en) Novel pyridoindoles
US3557127A (en) Substituted cyclohexenes,derivatives thereof and processes for obtaining same
US3459767A (en) Aminomethylindoles
US3449355A (en) 2-((3,4-dihalophenoxy)methyl)-2-imidazoline
US3946012A (en) 6-L-dihydroxyethyl-2,4,7-trioxo-8-D-ribityl pteridine and process for producing the same
US3530126A (en) N-heterocyclic substituted cyclohexanes
US3775479A (en) Amine compounds
US3345376A (en) Polyhydro-6-methoxy-1-(3, 4, 5-trimethoxyphenyl)-9h-pyrido[3, 4-b]indoles
US2914532A (en) Lower alkyl 4-phenyl-1-(3-phenylpropyl) piperidine-4-carboxylates and their preparation
US3202666A (en) Substituted 9h-pyrido (3-4-b) indole-1 carboxylic acid and derivatives
US3972931A (en) N,N'-Disubstituted benzamidines
US3647877A (en) Aminopropionanilides
DE2462967C2 (de) Derivate des 3-Amino-5-methyl-2-phenyl-pyrrols, deren Salze und diese enthaltende pharmazeutische Zubereitung
AT319936B (de) Verfahren zur Herstellung von neuen Phenylimidazolidinonderivaten und ihren Salzen
US3725419A (en) Quinuclidylalkyl esters
US3483209A (en) Aralkylamines
US3337546A (en) Certain 1, 3 oxazines and a process for their preparation
US3202671A (en) 2, 9-dimethyl-4-hydroxy-1, 2, 3, 4-tetrahydro-9h-pyrido [3, 4-b] indole and its acid addition salts
CH615153A5 (de)
EP0158312B1 (de) 1-[Cyclohexyl]-3,4-di-[hydro]-isochinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
US3452030A (en) 4-(n-isobutyrylanilino)-1-benzylpiperidine
US3423423A (en) 2-(2,4,5-trichlorobenzyl)-2-imidazoline
DE1668146C3 (de) N-substituierte S,S-Diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung